Choosing
- 4 years ago
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Choosing An Outfit. free porn video
Tammy was my next door neighbour when I grew up. We went to school together and were very good friends. She was beautiful, athletic and great natured, and would have been the perfect girl for me or indeed any guy. Alan was the son of my mums best friend, six months older than me so like Tammy we were at school together and because of our mums, we saw a lot of each other out of school too. Alan's parents had split up so he spent some weekends with his dad who was a big fan of the outdoors, so we often were out with him, camping, fishing and boating when Alan was at his dad's.
As we went into our teenage years and through puberty Tammy developed into an incredible looking quite tall and leggy young lady, Alan grew quite tall and strong. I kept slim and lithe through exercise and grew to a little lower than average height, which made me about the same as Tammy. Alan and I had a liking for heavy metal and hard rock so both grew our hair long.
Sadly at this time Tammy's mum died of cancer, She spent quite a lot of time with us as my parents helped her and her dad, Danny, get through this difficult time. We became very very close, the very best of friends. It was at this time that I realised that I was gay and enjoyed cross dressing, Tammy knew before I did really. All these years later she still teases me saying it was obvious as I was talking about the style and materials of her clothes, shoes and underwear, rather than ogling her or trying to spy on her private parts. She became comfortable enough to get undressed and clothed in my company and I never once thought it was odd.
My friendship with Alan was still strong and although he would profess to fancy Tammy he never pursued her or made a real effort to chat her up. Alan and I still did a lot of outdoor stuff together, sometimes with his dad and as we got older a lot more frequently just the two of us. I enjoyed the activities we took part in, but I also increasingly loved just being with him, and I soon realised that I had a crush on him.
As I spent more time with Tammy some of my mannerisms became a little more effeminate and I started to style my hair a little more deliberately, instead of being just long unkempt headbanger style, I had it shaped and spent time and money on it. Tammy helped teach me to dry, curl, and straighten it. We would put each others hair into ponytails, plaits and buns. She said that I was the best girlfriend she had ever had. One Saturday when Tammy's dad was at work, and Alan was at a family wedding I went next door to visit Tammy. She said that she was really pleased to see me as she wanted my help and to try something with her. I was intrigued and we went to her bedroom. Her wardrobe was open and there was a couple of outfits on her bed and she had all her make up and styling equipment out.
"I want you to stand there side on to my full mirror' she ordered, "oh you need to be barefoot too and might be best to take off your jeans too."
"Really?" I asked, "why?"
"Really, really," she said excitedly, "We have loads to do so please don't dally "
Seconds later I was stood in the middle of her room in just my tshirt and boxers. She stood directly behind me and balanced a book on our heads.
"What the heck are you doing?" I asked. The book fell as I moved to look.
"Keep still,"she ordered and repositioned the book.
I could feel her moving to look in the mirror.
"Great!" She said excitedly, "we are exactly the same height."
"And you have the same colour hair, similar length too, eyes as well. You are perfect!"
"Well I have been working out." I said sarcastically.
"Don't be silly, you wally, I need you to be a model me and you are the best fit possible."
I had no idea what she meant by that but I was caught up in her excitement and started to get a buzz.
"You will need to take your t-shirt off" she told me, "and I want you to put this on."
She handed me a black and white Mary Quant style dress.
"Are you for real?" I asked.
"Yes,"she sighed, "look I am going to that wedding reception tonight and I want to look my best, you are virtually my body double and my very best friend, so I will check how you look in my choices and as I can look at you from all angles I can make a better decision. So put on my dress and let me see whether it is going to be the one for tonight."
My jaw dropped, I couldn't believe what she was asking, however, I was excited to start, and almost ripped my top off. I pulled the dress on and Tammy zipped it up. I looked in the mirror and immediately felt great, I did look a little like a girl.
"It doesn't sit right." Said Tammy.
I looked again, it seemed creased around the middle and loose at the chest.
"Boxers!" She stated, "take them off""
"I can't stand around here with no undies on!" I exclaimed.
"You're right." She agreed, "and I don't want your dirty bits rubbing on all my best outfits."
"Oi! I have showered" I retorted.
"Hmmm, maybe," she laughed, "oh I've an idea"
With that she went to a chest of drawers.
"Put these on, this will do the trick." She said, "oh and try to tuck your cock down, it will make things flatter."
With that she gave me a pair of pink cotton briefs with a thin white lace trim, I took them from her and stared at them, then at her, then back at the panties.
She pleaded with me to put them on. Sighing I took off the dress and then my boxers. I slipped the briefs up my leg, I trembled a little as I pulled them over my butt, it felt fantastic putting them on. I adjusted my boy bits and pulled them up tight, I caught a glimpse in the mirror and couldn't help but smile and get even more excited. Tammy once again helped me into the dress, it definitely looked better around the waist. I turned and twisted and moved to Tammy's command, trying to look at myself in the mirror at the same time. I felt incredible. This time I was even more girly looking.
"Something is still not quite right." Pondered Tammy, my confidence slipped a little, as I was starting to think I looked good.
"Got it!" She exclaimed, returning to the chest of drawers, she then went to her dressing table for a few minutes.
"Dress off, this on, then we shall try the dress again." She ordered me again, "sorry it does not match the knickers."
Once again I looked at her offering, it was a white bra, the cups were carefully stuffed with cotton wool. The bra was quite plain, but the material felt lovely.
"I think them not matching is the least of my worries." I stated dryly.
"When you have them boys coming to call, you'll be wanting it all to match," she said saucily, "trust me, details matter."
I blushed at the thought of being in lingeried in another boy's company, but at the same time was thrilled at the thought too.
Once again I removed the dress, Tammy showed me how to put the bra on properly and in moments the dress was back on.
Tammy nodded her head in approval, as once again she had me turn and pose. This time when I looked at the mirror, there was definitely a very feminine figure in the reflection. I was excited beyond description and felt completely different in an amazingly free and exhilarating way.
She liked the dress on me, it was going to need hosiery and the right shoes but it could be the one. I thought I looked sexy in a sophisticated way, but it was now time to try the next outfit.
Off came the black and white number on went a rah rah skirt combo (this was the 80's remember). This made my bum look big according to Tammy, I thought it was fun and girly, but not as classy as the first dress.
Then it was a skirt, jacket and blouse, three different blouses to be precise and two skirts. Tammy felt that they were too formal, I thought I looked ready to go to the office or teach a lesson, both scenarios excited me. A jersey dress next, apparently not dressy enough according to her, I agreed but thought it would be nice to wear all day, if ever I had an opportunity to do so.
A long skirt with a high slit up the side was deemed too slutty, we laughed when I stated that was the reason I liked it. Tammy called me a tart and said that she would bet that Alan would like to run his hand under it and over my thighs. I went bright red at the thought and once again she laughed at my obvious embarrassment.
"Do not tell me that you have not thought about it." She scoffed, "I bet he has."
"I may have," I laughed back, "I hate that you know me so well, Alan may have thought about doing it to you I only wish I was in his thoughts."
"I really cannot believe that you are still so blind and naive." She replied, shaking her head, "the little black and white dress it is, now will it be black or white tights?"
I was down to the bra and panties as Tammy got some tights out. I got quite excited thinking about putting them on with them.
"You can't wear these with your legs in that condition." said Tammy.
"What is wrong with them?" I replied disappointed.
"Hair!" She stated.
"They're not that bad."
"For a boy, they are not very hairy I will grant you, my legs would probably be the same if I didn't wax or shave, but, I do wax and shave, so must you."
Not for the first time my chin hit my chest in astonishment. Was she serious? Most definitely, as moments later we were in the bathroom and my legs were lathered in shaving cream. We did not have time to wax, but I was to be shown how to do that next time! I was nervous shaving my legs even though I had been shaving my face for a while. The panties were off so that I could do my bikini line and my bra removed too, so my armpits and few chest hairs could succumb to the razor's edge.
We returned to the bedroom and I put my bra and panties back on, I had been wearing them for so long that I considered them mine now. Tammy gave my nails a quick touch up with the file, but, I had been keeping my nails done for some time now so it was only a brief buffing. She then proceeded to guide me in how to put a pair of tights on without snagging or tearing them, and ensuring that they are on comfortably with no twists and fitting snugly. The feeling of the nylon unrolling up my legs squeezing over my skin and clinging to my thighs and buttocks was once again incredible. At that time it was the most wonderful sensory experience of my life, it actually caused me to gasp and tremble. Tammy joked that she thought Iwas going to orgasm. I almost admitted to her that so did I.
We tried the white tights with the dress first, I looked into the mirror and was certain that the image smiling back to me was all woman. I felt so natural and right.
"One last thing missing." said Tammy, "what shoe size are you?"
"Seven." I replied
"Damn I am a six." She paused for thought. "Hold on, come with me."
We went into the spare bedroom where there were a couple of suitcases and boxes. Tammy explained that they contained her mum's clothes, but after packing them away, her dad could not actually bring himself to throw them away. Her mum had been similar to Tammy, just a little heavier and as it turns out a whole shoe size bigger. Tammy went into a couple of boxes before pulling out two pairs of black court shoes, one pair with a long heel the other a smaller kitten heel. Both similar to ones she had herself. I was made to put the shorter heel on and walk back to the bedroom. Another new sensation another incredible and natural feeling of pleasure as I walked as elegantly as I could. I looked in the mirror and almost cried with pleasure at the amazing sight reflected back at me I was definitely all woman now.
"I am certain that is the outfit tonight." Tammy sounded pleased. "But, I would like you to try on these high heels just to check and it will give you a go at them."
I slipped them on, they made my legs and feet look even more elegant. At this point I was still sitting down. I sttod up a bit wobbly, but soon got my balance. Tammy was right they did not suit the dress, but, they looked and felt incredible.
"I think you should keep them." Tammy offered, "they look good on you and you should practice walking in them."
"Thanks," I whispered. A tear rolled down my cheek. "This has been a brilliant day, I cannot describe how fantastic I feel right now."
"You daft bitch," she replied, "come here."
We embraced and both of us sobbed a little.
We recovered soon and Tammy told me to keep both pairs of shoes, they were too big for her and her dad would not notice
Just then the main door opened and Tammy's dad, Brian, announced that he was home.
"Shit!" We both said together.
"Quick put your jeans and tshirt on." Whispered Tammy.
"You upstairs Tammy?" Shouted Brian.
"Yes, just choosing an outfit for tonight," she replied, "Jim is here too."
"Cool, I shall come see."
I had just got my top and jeans on when Brian started up the stairs.
"Cotton wool!" Hissed Tammy.
I had only just got it out of the bra when Brian's head poked round tbe door.
"You're wearing that new dress." He asked, "you will look amazing, we have an hour, if you want a shower before me best get in there now."
"Ok will do, I know how long you can take." Tammy laughed in reply and headed to the bathroom
Brian asked how I was and that he was sorry he had not seen me or my parents in some time, but he was just so busy at the moment. I liked Brian a lot he was a nice guy, handsome for an older fellow too. He was a roofer which meant he was strong and burly, grey flashes were beginning to show in his cropped dark hair. He had been very morose when his wife had died, however, now some months later, his sparkling wit was beginning to return, which was evident in the short conversation we had. I must admit that I quite fancied Brian, and had fantasies about him. Right now though I was conscious that I had a bag in my hand with two pairs of his wifes shoes and was wearing his daughters underwear, I thought that he was bound to figure it very soon, so I made my excuses to leave them to get ready. I got out of the house as quickly as possible and shouting a quick hello as I entered my house I headed straight for my room.
My intention was to get out of the the tights bra and panties as soon as I could, but, I caught a glimpse of myself in my wardrobe mirror and was once again transfixed by my reflection and how feminine I was. I could hear mum in the kitchen and the football results so knew that my parents were unlikely to disturb me for some time. I got the heels out of the bag and slipped them on. They looked and felt incredible. I wobbled around the room on them for a moment, then sat on the edge of my bed. I crossed and uncrossed my legs enjoying the sensation as my nylon clad thighs rubbed together. I rubbed my hand up my thigh and over my buttocks, imagining that it was Brian's rough large manly hand. I squeezed my bum, I rubbed my groin. A tingle started deep in me, my arse twitched, my balls tightened my back arched and I called Brian's name as my sperm spilled int my pink panties with the white lace trim.
I had just about got my jeans and tshirt back on when my mum called me down for dinner, I tucked my newly acquired underwear under the bed wondering how on earth I would get them clean and when I would next have a chance to wear them again. I then joined my parents for dinner at the end of what was a fantastic day
As we went into our teenage years and through puberty Tammy developed into an incredible looking quite tall and leggy young lady, Alan grew quite tall and strong. I kept slim and lithe through exercise and grew to a little lower than average height, which made me about the same as Tammy. Alan and I had a liking for heavy metal and hard rock so both grew our hair long.
Sadly at this time Tammy's mum died of cancer, She spent quite a lot of time with us as my parents helped her and her dad, Danny, get through this difficult time. We became very very close, the very best of friends. It was at this time that I realised that I was gay and enjoyed cross dressing, Tammy knew before I did really. All these years later she still teases me saying it was obvious as I was talking about the style and materials of her clothes, shoes and underwear, rather than ogling her or trying to spy on her private parts. She became comfortable enough to get undressed and clothed in my company and I never once thought it was odd.
My friendship with Alan was still strong and although he would profess to fancy Tammy he never pursued her or made a real effort to chat her up. Alan and I still did a lot of outdoor stuff together, sometimes with his dad and as we got older a lot more frequently just the two of us. I enjoyed the activities we took part in, but I also increasingly loved just being with him, and I soon realised that I had a crush on him.
As I spent more time with Tammy some of my mannerisms became a little more effeminate and I started to style my hair a little more deliberately, instead of being just long unkempt headbanger style, I had it shaped and spent time and money on it. Tammy helped teach me to dry, curl, and straighten it. We would put each others hair into ponytails, plaits and buns. She said that I was the best girlfriend she had ever had. One Saturday when Tammy's dad was at work, and Alan was at a family wedding I went next door to visit Tammy. She said that she was really pleased to see me as she wanted my help and to try something with her. I was intrigued and we went to her bedroom. Her wardrobe was open and there was a couple of outfits on her bed and she had all her make up and styling equipment out.
"I want you to stand there side on to my full mirror' she ordered, "oh you need to be barefoot too and might be best to take off your jeans too."
"Really?" I asked, "why?"
"Really, really," she said excitedly, "We have loads to do so please don't dally "
Seconds later I was stood in the middle of her room in just my tshirt and boxers. She stood directly behind me and balanced a book on our heads.
"What the heck are you doing?" I asked. The book fell as I moved to look.
"Keep still,"she ordered and repositioned the book.
I could feel her moving to look in the mirror.
"Great!" She said excitedly, "we are exactly the same height."
"And you have the same colour hair, similar length too, eyes as well. You are perfect!"
"Well I have been working out." I said sarcastically.
"Don't be silly, you wally, I need you to be a model me and you are the best fit possible."
I had no idea what she meant by that but I was caught up in her excitement and started to get a buzz.
"You will need to take your t-shirt off" she told me, "and I want you to put this on."
She handed me a black and white Mary Quant style dress.
"Are you for real?" I asked.
"Yes,"she sighed, "look I am going to that wedding reception tonight and I want to look my best, you are virtually my body double and my very best friend, so I will check how you look in my choices and as I can look at you from all angles I can make a better decision. So put on my dress and let me see whether it is going to be the one for tonight."
My jaw dropped, I couldn't believe what she was asking, however, I was excited to start, and almost ripped my top off. I pulled the dress on and Tammy zipped it up. I looked in the mirror and immediately felt great, I did look a little like a girl.
"It doesn't sit right." Said Tammy.
I looked again, it seemed creased around the middle and loose at the chest.
"Boxers!" She stated, "take them off""
"I can't stand around here with no undies on!" I exclaimed.
"You're right." She agreed, "and I don't want your dirty bits rubbing on all my best outfits."
"Oi! I have showered" I retorted.
"Hmmm, maybe," she laughed, "oh I've an idea"
With that she went to a chest of drawers.
"Put these on, this will do the trick." She said, "oh and try to tuck your cock down, it will make things flatter."
With that she gave me a pair of pink cotton briefs with a thin white lace trim, I took them from her and stared at them, then at her, then back at the panties.
She pleaded with me to put them on. Sighing I took off the dress and then my boxers. I slipped the briefs up my leg, I trembled a little as I pulled them over my butt, it felt fantastic putting them on. I adjusted my boy bits and pulled them up tight, I caught a glimpse in the mirror and couldn't help but smile and get even more excited. Tammy once again helped me into the dress, it definitely looked better around the waist. I turned and twisted and moved to Tammy's command, trying to look at myself in the mirror at the same time. I felt incredible. This time I was even more girly looking.
"Something is still not quite right." Pondered Tammy, my confidence slipped a little, as I was starting to think I looked good.
"Got it!" She exclaimed, returning to the chest of drawers, she then went to her dressing table for a few minutes.
"Dress off, this on, then we shall try the dress again." She ordered me again, "sorry it does not match the knickers."
Once again I looked at her offering, it was a white bra, the cups were carefully stuffed with cotton wool. The bra was quite plain, but the material felt lovely.
"I think them not matching is the least of my worries." I stated dryly.
"When you have them boys coming to call, you'll be wanting it all to match," she said saucily, "trust me, details matter."
I blushed at the thought of being in lingeried in another boy's company, but at the same time was thrilled at the thought too.
Once again I removed the dress, Tammy showed me how to put the bra on properly and in moments the dress was back on.
Tammy nodded her head in approval, as once again she had me turn and pose. This time when I looked at the mirror, there was definitely a very feminine figure in the reflection. I was excited beyond description and felt completely different in an amazingly free and exhilarating way.
She liked the dress on me, it was going to need hosiery and the right shoes but it could be the one. I thought I looked sexy in a sophisticated way, but it was now time to try the next outfit.
Off came the black and white number on went a rah rah skirt combo (this was the 80's remember). This made my bum look big according to Tammy, I thought it was fun and girly, but not as classy as the first dress.
Then it was a skirt, jacket and blouse, three different blouses to be precise and two skirts. Tammy felt that they were too formal, I thought I looked ready to go to the office or teach a lesson, both scenarios excited me. A jersey dress next, apparently not dressy enough according to her, I agreed but thought it would be nice to wear all day, if ever I had an opportunity to do so.
A long skirt with a high slit up the side was deemed too slutty, we laughed when I stated that was the reason I liked it. Tammy called me a tart and said that she would bet that Alan would like to run his hand under it and over my thighs. I went bright red at the thought and once again she laughed at my obvious embarrassment.
"Do not tell me that you have not thought about it." She scoffed, "I bet he has."
"I may have," I laughed back, "I hate that you know me so well, Alan may have thought about doing it to you I only wish I was in his thoughts."
"I really cannot believe that you are still so blind and naive." She replied, shaking her head, "the little black and white dress it is, now will it be black or white tights?"
I was down to the bra and panties as Tammy got some tights out. I got quite excited thinking about putting them on with them.
"You can't wear these with your legs in that condition." said Tammy.
"What is wrong with them?" I replied disappointed.
"Hair!" She stated.
"They're not that bad."
"For a boy, they are not very hairy I will grant you, my legs would probably be the same if I didn't wax or shave, but, I do wax and shave, so must you."
Not for the first time my chin hit my chest in astonishment. Was she serious? Most definitely, as moments later we were in the bathroom and my legs were lathered in shaving cream. We did not have time to wax, but I was to be shown how to do that next time! I was nervous shaving my legs even though I had been shaving my face for a while. The panties were off so that I could do my bikini line and my bra removed too, so my armpits and few chest hairs could succumb to the razor's edge.
We returned to the bedroom and I put my bra and panties back on, I had been wearing them for so long that I considered them mine now. Tammy gave my nails a quick touch up with the file, but, I had been keeping my nails done for some time now so it was only a brief buffing. She then proceeded to guide me in how to put a pair of tights on without snagging or tearing them, and ensuring that they are on comfortably with no twists and fitting snugly. The feeling of the nylon unrolling up my legs squeezing over my skin and clinging to my thighs and buttocks was once again incredible. At that time it was the most wonderful sensory experience of my life, it actually caused me to gasp and tremble. Tammy joked that she thought Iwas going to orgasm. I almost admitted to her that so did I.
We tried the white tights with the dress first, I looked into the mirror and was certain that the image smiling back to me was all woman. I felt so natural and right.
"One last thing missing." said Tammy, "what shoe size are you?"
"Seven." I replied
"Damn I am a six." She paused for thought. "Hold on, come with me."
We went into the spare bedroom where there were a couple of suitcases and boxes. Tammy explained that they contained her mum's clothes, but after packing them away, her dad could not actually bring himself to throw them away. Her mum had been similar to Tammy, just a little heavier and as it turns out a whole shoe size bigger. Tammy went into a couple of boxes before pulling out two pairs of black court shoes, one pair with a long heel the other a smaller kitten heel. Both similar to ones she had herself. I was made to put the shorter heel on and walk back to the bedroom. Another new sensation another incredible and natural feeling of pleasure as I walked as elegantly as I could. I looked in the mirror and almost cried with pleasure at the amazing sight reflected back at me I was definitely all woman now.
"I am certain that is the outfit tonight." Tammy sounded pleased. "But, I would like you to try on these high heels just to check and it will give you a go at them."
I slipped them on, they made my legs and feet look even more elegant. At this point I was still sitting down. I sttod up a bit wobbly, but soon got my balance. Tammy was right they did not suit the dress, but, they looked and felt incredible.
"I think you should keep them." Tammy offered, "they look good on you and you should practice walking in them."
"Thanks," I whispered. A tear rolled down my cheek. "This has been a brilliant day, I cannot describe how fantastic I feel right now."
"You daft bitch," she replied, "come here."
We embraced and both of us sobbed a little.
We recovered soon and Tammy told me to keep both pairs of shoes, they were too big for her and her dad would not notice
Just then the main door opened and Tammy's dad, Brian, announced that he was home.
"Shit!" We both said together.
"Quick put your jeans and tshirt on." Whispered Tammy.
"You upstairs Tammy?" Shouted Brian.
"Yes, just choosing an outfit for tonight," she replied, "Jim is here too."
"Cool, I shall come see."
I had just got my top and jeans on when Brian started up the stairs.
"Cotton wool!" Hissed Tammy.
I had only just got it out of the bra when Brian's head poked round tbe door.
"You're wearing that new dress." He asked, "you will look amazing, we have an hour, if you want a shower before me best get in there now."
"Ok will do, I know how long you can take." Tammy laughed in reply and headed to the bathroom
Brian asked how I was and that he was sorry he had not seen me or my parents in some time, but he was just so busy at the moment. I liked Brian a lot he was a nice guy, handsome for an older fellow too. He was a roofer which meant he was strong and burly, grey flashes were beginning to show in his cropped dark hair. He had been very morose when his wife had died, however, now some months later, his sparkling wit was beginning to return, which was evident in the short conversation we had. I must admit that I quite fancied Brian, and had fantasies about him. Right now though I was conscious that I had a bag in my hand with two pairs of his wifes shoes and was wearing his daughters underwear, I thought that he was bound to figure it very soon, so I made my excuses to leave them to get ready. I got out of the house as quickly as possible and shouting a quick hello as I entered my house I headed straight for my room.
My intention was to get out of the the tights bra and panties as soon as I could, but, I caught a glimpse of myself in my wardrobe mirror and was once again transfixed by my reflection and how feminine I was. I could hear mum in the kitchen and the football results so knew that my parents were unlikely to disturb me for some time. I got the heels out of the bag and slipped them on. They looked and felt incredible. I wobbled around the room on them for a moment, then sat on the edge of my bed. I crossed and uncrossed my legs enjoying the sensation as my nylon clad thighs rubbed together. I rubbed my hand up my thigh and over my buttocks, imagining that it was Brian's rough large manly hand. I squeezed my bum, I rubbed my groin. A tingle started deep in me, my arse twitched, my balls tightened my back arched and I called Brian's name as my sperm spilled int my pink panties with the white lace trim.
I had just about got my jeans and tshirt back on when my mum called me down for dinner, I tucked my newly acquired underwear under the bed wondering how on earth I would get them clean and when I would next have a chance to wear them again. I then joined my parents for dinner at the end of what was a fantastic day
Jayla
- 12.09.2021
- 14
- 0
